Virgin Territory
by Mindy35
Summary: Jack/Liz. How did Jack know when Liz became a woman?


Title: Virgin Territory

Author: Mindy

Rating: K+ sexual concepts.

Disclaimer: Tina is queen of all.

Pairing: Jack/Liz

Spoilers: "Larry King".

Summary: How did Jack know when Liz became a woman?

-x-x-x-

Jack brushed her knee with his fingertips: "Come on, tell me."

"No."

"We're drunk, this is what you do when you're drunk."

"We're not that drunk. I can still form sentences."

"So form a few and tell me."

"No, Jack. It's embarrassing."

"The story is embarrassing or telling me is embarrassing?"

Liz grimaced and recrossed her legs: "Both."

His eyes glinted mischievously at her. "If you tell me yours, I'll tell you mine."

"I'll bet," she muttered into her glass.

"It's a good story," he coaxed in his most compelling voice: "And I tell it _very_ well."

Her eyes skimmed the quietly bustling bar: "Mm, I'm sure it's like something straight out of Henry Miller."

"See?" he teased, leaning in to capture her gaze: "You _want_ to know."

She leant back on her barstool, hand curled round her drink. "Actually, I was never a Henry Miller fan."

"I don't believe you," Jack rasped.

"It's true," she shrugged one shoulder: "I couldn't finish one of his books."

"That's not really what I meant," he smiled, then added slyly: "Be honest, Lemon. Aren't you the least little bit curious?"

Liz's gaze finally met his, brown eyes tipsy and scathing. "This may sound odd to you, Jack, but hearing how you lost your virginity is probably only marginally more appealing to me than telling you how I lost mine. Which is not at all."

"Fair enough, Lemon, fair enough." Jack held up both hands, retreating into his seat. "Knowing you the way I do, I dare say I can probably guess at the basic details anyway."

"Oh, you think so, do you?" she muttered with more than a hint of doubt in her tone.

"Certainly. For instance," he countered, calm and confident: "I happen to recall that you did not have a steady boyfriend in high school--"

"That's because high school boys are gross," she interjected.

"So you've said." He sent her a lazy, lethargic grin: "Which means it had to have taken place…first year college. Am I right?"

"_Wrong_," she retorted, tone unapologetically obnoxious: "Ha! And you think you know me so well."

"Okay then…" Jack studied her momentarily, then wiggled his fingers in the air: "aahh, _some time_ during college…I see…a fresh faced Liz Lemon…in a baggy woollen sweater--"

"I was never fresh-faced, Jack," she interjected again: "I had mild acne up until…well, last year, actually."

Jack continued regardless, weaving his version of events: "I imagine you had little interest in college boys--"

She tilted her head. "They had little interest in me."

"They probably just confided in you about their girlfriends back home," he went on, eyes never leaving her face: "and invited you to parties where you hid in a corner and ate cheese."

"Never invited," she sighed: "never went."

"So, instead…" he mused, a whimsical little smile on his face: "young Liz Lemon developed an all-consuming crush on one of her professors."

Her eyes cut to his. "What now?"

"After some…flirtatious denial, you both gave into the forbidden attraction--"

She snorted loudly. "Are you kidding me? First of all, Jack, most of my tutors were ladies--"

"Really?" He raised his brows: "That certainly puts a different spin on events."

"Secondly, dude--" she made a face, leaning across to hit him: "this is not one of your imported pornos, okay? This is _my life_ we're talking about."

He smiled broadly, picking up his drink and swirling it in the glass. "I am simply attempting to fill in the gaps. If our friendship is to progress, Lemon, we must at some point trust one another with the details of our respective pasts and since you will not tell--"

"It _wasn't _at college," she blurted out, her eyes dropping to her lap: "It was……"

The wait was interminable.

She gulped. "…afterwards."

"_After _college?" he repeated, unable to keep some surprise from his voice. A moment later, he asked rather cautiously: "How old _were_ you?"

She rolled her eyes, pulling her skirt over her knees: "I'm not telling you that, you'll laugh."

"If I promise not to laugh--"

"You will. You won't be able to help yourself."

Jack held up a hand. "I swear, on my mother's life, which as you know is unrelenting and unmerciful."

She shot him a glare from beneath her lashes, let out a deep sigh, then admitted: "It was…after…I moved to Chicago."

Jack looked like he was doing the math in his head. "You moved to Chicago when you were…twenty-two, right?"

She nodded, took a sip of her drink. "Right."

"So you were, what?" He gave a shrug: "Twenty-two?"

Liz took another sip.

"Twenty-three?"

She took another.

"Twenty-three and a half?"

She took a long sip. "Twenty-five."

"Twenty-five?" Jack nodded his head a few times: "You…became a woman at…twenty-five years old?"

She stuck out her tongue. "Yeesh, I hate that euphemism."

"Well. That's…" Jack paused for a long time: "not so...late."

"Yeah, right," she commented, her voice rich with sarcasm.

"So…"

There was another pause.

"Why'd you wait so long then?" he asked eventually.

She gave a wry laugh. "The offers were not exactly pouring in, Jack."

He grinned groggily, lowering his voice. "Now, I find that very hard to believe."

She narrowed her eyes in return. "No, you don't."

"Surely," he shrugged: "surely, there must have been _someone_?"

"Well, there wasn't -- up til then, okay? So!" She waved a hand, the hand with the drink in it, spilling some on herself: "There you go -- now you know. Time for another drink."

He held out a hand: "Wait. Hold a second…. Who was it?"

"What?"

"Who…" he raised his eyebrows pointedly: "did the deed?"

She screwed her nose up, searching for the barman. "Who cares?"

"Boyfriend?" he persisted.

"_Yes, boyfriend_," she answered testily: "Can you imagine me with my fuzzy hair and my prolonged puppy-fat picking up some random guy to…"

"Pop your cherry?" he offered.

One hand flew up to cover her face, her eyes snapping shut. "Shut up, shut up, shut up--"

Jack smiled in unrestrained glee. "I'm learning so much more about you tonight."

"_Too_ much," she moaned pitifully. She opened her eyes, her hand flapping between them: "This is too much sharing, Jack."

"Tell me, Lemon, I'm interested," he went on, smile still in place, despite her tortured look: "Was this your _first _serious boyfriend?"

"Augh…" She dropped one elbow to the bar, slumping against it with her forehead in her hand. "Maybe…" she answered evasively.

"And," his eyes widened in curiosity: "…how was it?"

"Brief and disturbing," she replied, deadpan. "Just like this conversation. I'm hoping. Can we move on now? Talk about taxes or something?"

"Wait, wait, wait--" he urged, face all lit up: "one more question. Then I promise you--" he made a zipping motion across his lips.

She glared up at him. "What?"

"What was his name?"

"His name?"

"The man who--?"

She put up a hand. "Yeah-yeah, I got it."

"Did you love him?"

She stalled momentarily: "You said one question," then before he could interrupt, answered: "And his name was…Russell."

Jack's eyes twinkled. "Russell?"

"You promised not to laugh," she warned.

"Russell…? Oh, Lemon…" He reached out to pat her knee again, his expression sympathetic: "it must have been terrible for you."

She pouted sullenly. "You can't assume that, just from his name."

"Ah, yes," he rasped: "yes, I can."

"Hey--" she informed him sharply: "Russell cared about me. Deeply. He just…cared about…other things more."

"What other things?" Jack murmured: "Other guys, maybe?"

Liz shifted in her seat. "Alright!" she announced abruptly: "time for your story."

Jack took up his drink, watching her over its rim. "I thought you didn't want to hear it."

"I don't," she muttered, stabbing at some ice with her straw: "But it can't be worse than telling you mine--"

"In truth, you divulged very little," he pointed out.

"But what I did was excruciating. And I am all for reciprocity." She gestured again for the bartender: "Plus, I'm gonna have another drink so...."

She waited until both of them had fresh glasses placed in front of them, on fresh new napkins, before sitting back in her seat and crossing her arms over her chest: "Okay. Begin. This better be good."

Jack's mouth twitched upwards. "You know, you're not the first woman to utter those words to me with such an alluring look of challenge in her eye."

Her face immediately lost its composure. "Ew, Jack, over-share! Jeez, do you not have _any_ boundaries?"

"I apologise." He smirked in satisfaction then began in a smoother than smooth tone: "It was the summer of my eighteenth year--"

Liz tilted her head. "Huh."

He stopped. "What?"

"Eighteenth?" she questioned: "_Really_?"

"I was raised a Catholic, Lemon," he told her justifyingly.

"I know, just…_eighteen_…" she gave a shrug: "seems kind of late. For you, I mean. I kind of had this picture of you chatting up girls in the sandpit."

He leant a little closer, voice low. "I'm not saying I hadn't done…other things before that age."

"Yeah, okay--" she waved a hand: "so you were eighteen. On with the story."

"I was eighteen," he repeated, with a brief nod: "She was…a little older."

"How much older?"

"A little older, Lemon, what does it matter?"

"It matters, Jack, it's integral to my unwilling enjoyment of your sex story."

He sighed then told her: "She was twenty-one."

"Woo-hoo," she hooted, raising a hand in the air: "Go Jackie-boy! Wait-wait-wait, no, lemme guess--!" the hand turned into a finger, poking his shoulder: "You met this chick at the country club, wooed her over Long Island iced teas then made your move on the twentieth hole?"

"There _is _no twentieth hole, Lemon, and she was no country club princess." He took a breath, telling her evenly: "My first happened to be the girl next door. Quite literally." He paused: "In fact--"

"_In fa-act_…?" she prompted, eyebrow arched.

He shrugged. "She used to babysit from time to time."

Her mouth fell wide open. "You…_nailed_ the babysitter?"

"She babysat my siblings, Lemon, not me."

"Oh. My. God."

Jack ignored her obvious amusement and went on with his story, tone waxing lyrical: "We grew up together. Knew each other all through school, spent holidays together. She was a funny looking thing, to be honest, bright red hair and freckles everywhere. Legs and arms for days. She kept tripping over them and knocking things over like she didn't know what to do with them."

Unintentionally, Liz had lent closer, her arm curled on the bar, her chin resting on her hand and her eyelashes dipping lazily as she listened. His eyes scanned her face as he shifted closer and continued:

"I remember she used to wear those tall white socks, you know? Pulled right up to her knees and she was always drawing, sketching in books. She'd always wanted to be an artist. Anyway, when she came home on a break from college, she'd…well…"

Her brow creased as his voice trailed off. "Developed…?" she guessed, making an exaggerated cupping gesture over her chest.

"No," he said, voice still languid and meditative: "No, no…softened. She'd got this…luminous look to her. Her clothes, her eyes, the way she moved and spoke and smiled. Everything about her was smooth and sweet and magical. Then one day…she asked me if she could sketch me."

Her eyes flicked over the length of him. "I'm assuming she meant…_all _of you."

"Indeed she did," he replied, glancing at her from beneath his brows: "One thing led to another, as you can imagine."

"I won't," she muttered: "if you don't mind."

Jack straightened in his seat, looking at her. "And, ah… the Lemon-rated version ends there."

She nodded a few times. "Hm…But, um…?"

"But, what?"

"Well, you know…" she shrugged, a small smile on her lips: "How was it?"

"How d'you think?" he simpered.

"You _really_ enjoyed it? _Really_?" She wagged her head confusedly: "God, who has a _good _first time?"

"I'm not saying there hasn't been improvement since then," Jack mused slowly: "but…I must say, it was…fairly memorable."

"What was her name?"

"Her name?"

"You remember this memorable girls name, don't you?"

"Of course." He took a sip of his drink. "…Betty."

"Bettie?" she repeated: "As in…Bettie Page?"

"No," he murmured lowly: "Betty as in…Elizabeth--"

She lifted an eyebrow.

"…Barrett Browning."

She ducked her head, suppressing a laugh. "Uh huh…D'you ever see her again?"

"Mmm, no…" he mused: "But I still have the sketch."

"Wow." Her eyes widened as she took a sip of her drink: "That…is creepy, Jack, genuinely twisted."

"As may this be--" He lent forward, peering at the napkin she swiped over her mouth.

"What?"

"There's a message," he said, holding it up for her to see: "For you, and from the bartender would be my guess."

She squinted at it then shook her head: "I can't read that without my glasses."

Jack took it, squinting himself. "It says…we-ell now…"

"What?"

"It says 'Russell was a lucky guy'."

Liz stopped breathing, her eyes going wide a second before she buried her face in her hands. "Oh God. Oh God, no. No-no-no-no-no…"

"It's alright, Lemon. Don't hyperventilate." Jack put his hand back on her knee and left it there: "You don't know this man, what does it matter--"

"What does it _matter_?" she moaned, rocking in her seat: "Jeez, Jack, I didn't even want to tell _you_ and now the _bartender_ knows the most embarrassing details of my sexual history!"

"Not all of them," he replied rationally: "I'm sure there's some you're not telling me."

"This is _all your fault_,' she hissed, quickly glancing over her shoulder: "Oh my God. He heard _everything_!"

Jack held out the napkin for her: "He left a name and number, if that makes you feel any better. Name's Mike and…do you want the number?"

She grit her teeth. "I do not."

"I must say," Jack mused, peering down the bar for the culprit: "that is fairly presumptuous of him."

Liz downed the rest of her drink. "You're telling me."

"How does he know _we_ are not together?"

"…Excuse me?"

Jack met her eyes, looking vaguely affronted himself. "He's got some nerve making a move on you right in front of me. He shouldn't assume we aren't a couple."

"Um, Jack," she informed him bitingly: "there's not a person in this bar who'd look at us and assume we are a couple."

"Why's that then?" He ran an eye over her black dress and high heels: "You look very presentable tonight, Lemon. Why couldn't we be together?"

She eyed him askance: "God, you really must be drunk if y_ou're_ asking _me_ that."

"These people don't know us," he went on, glancing about the bar: "That insolent, glorified servant doesn't know either of us. Why shouldn't he or they assume that I am a man with a profound weakness for chronically slouched, slightly abrasive, carnally challenged, thirty-something wallflower-types? And _you_ have an obscene and desperate weakness for--"

Liz raised a hand. "Yeah, I'm going to stop you right there."

"Well?" he insisted, taking another look at the bar's inhabitants: "Why shouldn't they?"

She brushed some imaginary lint off her dress. "Oh come on, it's obvious."

"Not all couples are obvious," Jack retaliated mildly. "Perhaps we were set up on a blind date. Perhaps I was told you have a good personality."

Her eyes narrowed. "Perhaps I was told you were charming."

"Exactly," he nodded: "Perhaps neither of us was disappointed."

She shot him a look as she rose onto the rung of her stool. "Well, I dunno, Jack. Maybe barman _Mike_ thinks you're too old for me."

"What are you doing?" he asked, brow crumpled.

She looked over her shoulder at him. "I'm calling him over here."

"Then what're you planning on doing?" he muttered: "Ordering a screaming orgasm?"

"No way," she told him, waiting for her secret admirer to finish serving before catching his eye. "I could never date someone who eavesdrops. Could you imagine? You'd never have any privacy. What if I wanted to order pizza in the middle of the night? Would I then have to share it with him?"

Behind her back, Jack eyes slid over her as she lent over the bar, calves flexed. "So, what're you going to say to him?"

"Well, Jack," she said, plopping back into her seat: "I'm going to very politely tell him that you're my live-in boyfriend and _you _are going to be very convincing when I do."

"I'm your boyfriend?" he asked doubtfully: "Who doesn't know how you lost your virginity?"

"I'm very private," she replied: "and we haven't been dating long."

"Yet we're living together," he pointed out: "Must be love."

"Nope." She sucked on her straw then pointed it at him: "You got evicted. You couldn't pay your rent and I took you in."

Jack scoffed. "No one in this bar would believe I can't afford rent."

She spread her hands, leaning forward: "Maybe you gamble, who knows? Maybe, you drink all your dough away, I dunno. Maybe, I'm the only good thing in your life, the only thing that keeps you on the straight and narrow. Maybe, I'm your reason for living."

"In that case," he answered swiftly: "I think we should get married."

She shot him a sideways glance: "Not until you get your life in order," then turned to greet the approaching barman, her tone poisonously sweet: "Hi there, Mike, is it? I got your note and I just wanted to introduce you to my boyfriend."

Jack stood, plastered a grin on his face and slung an arm about her waist. "Fiancee."

"Right. Whatever." She toppled down off her stool, stabbing a finger at his tie: "My fiancee, Jack."

"Oh." Mike cleared his throat and glanced between the two of them: "Hi." He gestured to Liz's hand: "I…didn't see a ring."

Jack lent forward, whispering conspiratorially. "She's very fussy."

Liz dug her finger deeper into his ribcage. "He can't afford one."

Mike smiled falteringly. "I'm sorry. I really didn't think you were _with_….each other. I usually have an eye for these things."

"We get that _a lot_," she nodded emphatically: "you know, because of the _massive _age difference."

Jack tugged her tighter into his side, looking down at her. "Well, she may not be the obvious choice, my Le--"

"Elizabeth."

"Elizabeth. But she makes my miserable life worth living. Right, Pumpkin?"

"Right." She captured the arm he had around her, tugging on it: "So, nice to meet you…we're going to go now, and--"

"Roger each other senseless," Jack finished with a cheerful nod.

Liz forced a smile. "That's the plan."

Mike raised a hand, face confused. "Nice to meet you…"

"You too," Jack lent back in and squeezed the man's hand, growling out his name: "Miiike."

Liz yanked on his arm, stumbling towards the door. "Stop glaring, Jack."

"I won't," he grunted.

"Cut it out," she hissed.

Jack continued to glare as he was hauled towards the exit. "This is what I would do if he tried to steal my future wife. I'm simply being authentic to my role."

"You're being an ass, is what," she muttered, under her breath.

Eyes still fixed on the other man, he drew in a deep breath as they reached the door. "Of course he is right about one thing. I will give him that."

Liz retrieved his coat from the rack and shoved it at him: "What?"

"Russell."

She stooped to pick up her dropped hat. "Huh?"

"Didn't know how lucky he was," he said, eyes turning on her as she rose from the floor.

For a moment she looked like her head was spinning. "You're drunk," she mumbled, one hand going to her forehead: "And I'm drunk…"

Jack reached behind her for her coat, his mouth coming dangerously close to hers. "Doesn't make it any less true."

She held her breath, her eyes locking with his. Then as he shook out her coat, she turned her back and allowed him to slip it on her.

"Actually…" she told him quietly: "the last time I saw Russell he knew exactly how lucky he was. He's married to a lovely man called Phil and they own a stationery shop in Vermont."

Jack's voice was low and warm, close to her ear. "Your time will come, Lemon."

She turned round to face him, pulling her hat over her hair. "My time?"

His eyes were heavy-lidded and tender as he swayed into to her. She put out both hands, stopping him from tipping forward. Jack looked down at the hands pressed into his body, then raised his gaze back to her face.

"One day," he told her: "I'm sure of it; you will find yourself the perfect mate, worthy of all your exceptional qualities, and capable of giving you, perhaps even daily, _multiple_ screaming orgasms."

She let out a low, shy chuckle then reached up to give his cheek a sloppy pat with her gloved hand: "Well, that is…some kind of sweet, Jack, thankyou."

"And when you do, Lemon," he added solemnly, placing his hand over hers: "when you do…I'll be there."

She blinked at him through her alcohol haze. "See, now, you didn't need to add that last part. 'Cause that went some place weird."

Jack merely grinned as he took the hand on his face and looped it through his arm. Then he pushed through the door out into the cold night. Liz shuffled closer as the winter wind hit them, her face turned into his shoulder. And what neither of them knew was that, in that little moment by the door, anyone watching would've assumed them a couple. And very, very much in love.

_END._


End file.
